OFFBounds Retail

AI is making it easier than ever to build new technology, but also harder to know which companies will still matter tomorrow. In this episode, I speak with Miguel Bagulho, Investment Director for Retail Technology at Bright Pixel Capital, the technology investment arm of Sonae, about how investors identify startups with real long-term potential in such a fast-moving market.

We explore what makes retail technology defensible, why solving a measurable business problem matters more than the technology itself, and how retailers should approach the decision to build or buy. Miguel also shares where he sees the biggest opportunities ahead, from AI-native software and robotics to the technologies transforming pricing, inventory, procurement, and supply chains.

What makes someone leave a career on Wall Street to build a menswear brand with no experience in fashion? In this episode, I sit down with Alfré Snower, founder and CEO of Le Alfré, to hear how he transformed four shirts, a small New York apartment, and a lot of persistence into a growing lifestyle brand. He shares the reality of building from scratch, from personally messaging potential followers on Instagram to teaching himself design, manufacturing, content creation, and e-commerce.

We also explore how Alfré created an entire universe around the brand, culminating in Alfré’s Penthouse, a reservation-only retail destination in New York City. Our conversation covers intuition, vulnerability, creativity, and the importance of taking risks that established brands might avoid. More than a story about clothing, this is a conversation about believing in yourself, learning through failure, and building a brand that makes people feel something.

What if all your health records lived in one place, and AI could help you understand what they actually mean? In this episode of OFFBounds, Paula Macaggi speaks with Tony Ambrozie, Chief Digital and Technology Officer at CVS Health and Health100, about the company’s vision for a simpler, more connected and more personalized healthcare experience.

Tony introduces Health100, an AI-powered platform designed to bring fragmented health information together while keeping consumers in control of their data. They also explore what healthcare can learn from Disney’s approach to customer experience, why AI transformation must begin with a real consumer problem, and how technology can remove complexity from the patient journey, sometimes without the patient even noticing.

In this OFFBounds Summer Rewind, Paula Macaggi revisits her conversation with Lauren Steinberg, Chief Digital Officer at Loblaw, Canada’s largest retailer. Lauren shares how Loblaw built its digital business like a startup within the enterprise, embraced the advantages of being a first mover, and scaled online grocery through experimentation, accountability, and technology designed to evolve with customer expectations.

The conversation explores the future of grocery retail, from AI-powered personalization and composable commerce to search, loyalty, and agentic shopping. With Loblaw now bringing grocery shopping into ChatGPT, Lauren’s insights offer a timely blueprint for how retailers can build strong digital foundations today and remain ready for the next wave of commerce innovation.

What does it take to lead retail innovation when technology is evolving faster than ever? In this OFFBounds Summer Rewind, Paula Macaggi revisits her conversation with Andrew Laudato, Chief Operating Officer of The Vitamin Shoppe and author of Fostering Innovation. Andrew explains why companies do not need a separate AI strategy, but a strong business strategy that uses AI and other technologies to solve real problems and better serve customers.

The conversation explores AI agents, composable commerce, technology leadership, and how retailers can build high-performing teams prepared for constant change. Andrew also shares why curiosity is becoming one of the most valuable skills for the next generation of leaders. Recorded before many of today’s AI conversations became mainstream, this episode feels less like a prediction and more like a practical roadmap for the future of commerce.

Can a purpose-driven brand scale without compromising its mission? In this OFFBounds Summer Rewind, Paula Macaggi revisits her conversation with Dusan Vujovic, President of North America at Tony’s Chocolonely, to explore how the company entered one of the world’s most competitive consumer categories and built a loyal following around its mission to make chocolate 100% exploitation-free.

Dusan shares how Tony’s expanded into major retailers including Walmart, Target, Costco, Whole Foods, and Kroger while using bold branding, supply chain transparency, and purpose as engines for growth. Now the subject of a Columbia Business School case study published through Harvard Business Publishing, Tony’s story offers a powerful lesson in brand building and proves that doing the right thing can also be good business.

This week on our Summer Rewind series, we're revisiting one of our favorite conversations from Singapore at NRF APAC with Ian Burl, Chief Retail Officer at Mecca, Australia's leading prestige beauty retailer. Long before "experiential retail" became an industry buzzword, Mecca was building stores centered on human connection, empathy, and memorable customer experiences. In this episode, Ian shares how the company has created a culture where customer stories matter more than short-term metrics, why investing deeply in frontline education pays dividends, and how emotion has become one of the retailer's greatest competitive advantages.

As AI reshapes commerce, Ian makes a compelling case that emotional intelligence will become even more valuable than technical intelligence. From designing stores that foster genuine human connection to using technology only when it enhances, rather than replaces, the customer experience, he offers a refreshing perspective on the future of retail leadership. Whether you're building stores, digital experiences, or leading teams, this conversation is a powerful reminder that in an increasingly automated world, the most meaningful competitive advantage is still profoundly human.

Retail leaders have access to more information than ever, but knowing what actually matters is a different challenge. In this episode of OFFBounds, Paula Macaggi sits down with David Katz, EVP & Chief Marketing Officer of Randa Apparel & Accessories, to explore how leaders can separate signal from noise and identify the shifts that could fundamentally change their businesses. Drawing from Randa’s unique position across manufacturing, wholesale, brands and retail, David looks beyond the obvious implications of major forces shaping the market today.

From GLP-1 adoption and America’s aging population to climate change, geopolitical instability and evolving consumer behavior, David reveals the secondary effects that businesses may be overlooking. He also shares how Randa uses scenario planning, behavioral economics and early indicators to challenge assumptions and prepare for changes before they fully appear in the data. At the heart of the conversation is a powerful idea: we don’t have a shortage of information, we have a shortage of interpretation.

This episode was brought to you by Rayon. As retail brands open stores across new markets, from New York to Paris, keeping design consistent while moving fast gets harder. Rayon is a collaborative, browser-based platform built for people who design spaces, helping retail teams create layouts, documentation, and standards in one place, so every new location stays on-brand without slowing the rollout. Visit rayon.design and sign up for free today.

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Veronica Beard has become one of fashion's most admired brands by taking a very different path to growth. In this episode of OFFBounds, Paula Macaggi sits down with CEO Stephanie Unwin to explore how the company built a loyal community before opening stores, expanded thoughtfully from New York to London and Paris, and created a brand that women genuinely connect with. From retail strategy to international expansion, Stephanie shares the decisions that shaped Veronica Beard's remarkable journey.

The conversation also dives into leadership, entrepreneurship, and the future of retail. Stephanie explains why profitable, long-term growth beats chasing rapid scale, how AI should enhance—not replace—human connection, and why understanding your customer remains the foundation of every successful brand. This episode offers timeless lessons on building a brand that lasts.

In this episode of OFFBounds, Paula Macaggi sits down with retail leader, five-time Top Retail Expert, NRF Top Voice, and Retail Women in Tech founder Shannon Flanagan to discuss the launch of her new book, Choose, Don't Chase Your Career. After being laid off four times between 2016 and 2024, Shannon shares how those experiences forced her to rethink success, identity, and the stories we tell ourselves about work. Together, they explore why career transitions are about far more than finding the next job—they're opportunities to redefine who we are and what truly matters.

The conversation dives into fear, comparison, burnout, financial insecurity, and the courage to pause instead of rushing into the next opportunity. Shannon explains why the traditional definition of success is no longer enough, how to recognize the "scripts" that shape our decisions, and why choosing purpose over chasing titles can lead to a more meaningful career and life. Whether you're navigating a layoff, considering a career change, or simply questioning what success looks like, this episode offers practical wisdom and an honest reminder that sometimes the greatest transformation happens in the space between chapters.

You can buy Shannon's book here!